JPH0553266B2 - - Google Patents
Info
- Publication number
- JPH0553266B2 JPH0553266B2 JP3048644A JP4864491A JPH0553266B2 JP H0553266 B2 JPH0553266 B2 JP H0553266B2 JP 3048644 A JP3048644 A JP 3048644A JP 4864491 A JP4864491 A JP 4864491A JP H0553266 B2 JPH0553266 B2 JP H0553266B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- photoreceptor
- charge transport
- groups
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 108091008695 photoreceptors Proteins 0.000 claims description 71
- -1 azo compound Chemical class 0.000 claims description 40
- 239000000126 substance Substances 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000011230 binding agent Substances 0.000 claims description 7
- 238000010030 laminating Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 18
- 238000000862 absorption spectrum Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000270666 Testudines Species 0.000 description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
- 239000010802 sludge Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- MCIARMBFBVAZDY-UHFFFAOYSA-N 2,3,4,5-tetraphenylthiophene 1,1-dioxide Chemical group O=S1(=O)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MCIARMBFBVAZDY-UHFFFAOYSA-N 0.000 description 2
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 2
- BZKRKPGZABEOSM-XMHGGMMESA-N 4-[(e)-2-[3-[4-(diethylamino)phenyl]-2-phenyl-3,4-dihydropyrazol-5-yl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1\C=C\C1=NN(C=2C=CC=CC=2)C(C=2C=CC(=CC=2)N(CC)CC)C1 BZKRKPGZABEOSM-XMHGGMMESA-N 0.000 description 2
- UZGVMZRBRRYLIP-UHFFFAOYSA-N 4-[5-[4-(diethylamino)phenyl]-1,3,4-oxadiazol-2-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)N(CC)CC)O1 UZGVMZRBRRYLIP-UHFFFAOYSA-N 0.000 description 2
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- GACNTLAEHODJKY-UHFFFAOYSA-N n,n-dibenzyl-4-[1-[4-(dibenzylamino)phenyl]propyl]aniline Chemical compound C=1C=C(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 GACNTLAEHODJKY-UHFFFAOYSA-N 0.000 description 2
- QYXUHIZLHNDFJT-UHFFFAOYSA-N n-[(9-ethylcarbazol-3-yl)methylideneamino]-n-methylaniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C)C1=CC=CC=C1 QYXUHIZLHNDFJT-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- NGQSLSMAEVWNPU-UHFFFAOYSA-N 1,2-bis(2-phenylethenyl)benzene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1C=CC1=CC=CC=C1 NGQSLSMAEVWNPU-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- AOLUMCPVEUKWBX-UHFFFAOYSA-N 1-[2-[2-[2-(2,4-dimethoxyphenyl)ethenyl]phenyl]ethenyl]-2,4-dimethoxybenzene Chemical compound COC1=CC(OC)=CC=C1C=CC1=CC=CC=C1C=CC1=CC=C(OC)C=C1OC AOLUMCPVEUKWBX-UHFFFAOYSA-N 0.000 description 1
- LFKNYYQRWMMFSM-UHFFFAOYSA-N 1-ethyl-9h-carbazole;formaldehyde Chemical compound O=C.N1C2=CC=CC=C2C2=C1C(CC)=CC=C2 LFKNYYQRWMMFSM-UHFFFAOYSA-N 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- MQFBWJOMLIHUDY-UHFFFAOYSA-N 2,3,4,5-tetraphenylthiophene Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 MQFBWJOMLIHUDY-UHFFFAOYSA-N 0.000 description 1
- FKNIDKXOANSRCS-UHFFFAOYSA-N 2,3,4-trinitrofluoren-1-one Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C([N+]([O-])=O)=C([N+]([O-])=O)C(=O)C3=CC2=C1 FKNIDKXOANSRCS-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- WDFBSMBVBUXHRP-UHFFFAOYSA-N 2-[2-(4-methylphenyl)-1-phenylethenyl]-n-phenylaniline Chemical compound C1=CC(C)=CC=C1C=C(C=1C(=CC=CC=1)NC=1C=CC=CC=1)C1=CC=CC=C1 WDFBSMBVBUXHRP-UHFFFAOYSA-N 0.000 description 1
- CUDANNOCLGTWLM-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)-n-[4-(2-phenylethenyl)phenyl]aniline Chemical compound CC1=CC=CC=C1N(C=1C(=CC=CC=1)C)C(C=C1)=CC=C1C=CC1=CC=CC=C1 CUDANNOCLGTWLM-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- CLQYLLIGYDFCGY-UHFFFAOYSA-N 4-(2-anthracen-9-ylethenyl)-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=CC2=CC=CC=C12 CLQYLLIGYDFCGY-UHFFFAOYSA-N 0.000 description 1
- PLVXCTLGYWKUAY-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethenyl)-n,n-diphenylaniline Chemical compound C=1C=CC2=CC=CC=C2C=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PLVXCTLGYWKUAY-UHFFFAOYSA-N 0.000 description 1
- GAYAMEKFIBYRJW-UHFFFAOYSA-N 4-(fluoren-9-ylidenemethyl)-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=C1C2=CC=CC=C2C2=CC=CC=C21 GAYAMEKFIBYRJW-UHFFFAOYSA-N 0.000 description 1
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 1
- VWEQSBRKYZRWPQ-UHFFFAOYSA-N 4-[2-(10-bromoanthracen-9-yl)ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=C(C=CC=C2)C2=C(Br)C2=CC=CC=C12 VWEQSBRKYZRWPQ-UHFFFAOYSA-N 0.000 description 1
- ZTYUDPDLRTYFCU-UHFFFAOYSA-N 4-[2-[2-[2-[4-(diethylamino)phenyl]ethenyl]phenyl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=CC=C1C=CC1=CC=C(N(CC)CC)C=C1 ZTYUDPDLRTYFCU-UHFFFAOYSA-N 0.000 description 1
- NEZCBMZHMQVZOD-UHFFFAOYSA-N 4-[2-[3-[4-(dimethylamino)phenyl]-2-phenyl-1,3-dihydropyrazol-5-yl]ethenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)N(C)C)N(C=2C=CC=CC=2)N1 NEZCBMZHMQVZOD-UHFFFAOYSA-N 0.000 description 1
- HXOZSIAZPFUUHH-UHFFFAOYSA-N 4-[2-[4-[5-[4-[2-[4-(diethylamino)phenyl]ethenyl]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]ethenyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=C(C=2OC(=NN=2)C=2C=CC(C=CC=3C=CC(=CC=3)N(CC)CC)=CC=2)C=C1 HXOZSIAZPFUUHH-UHFFFAOYSA-N 0.000 description 1
- JJQOKUCYWIGCIN-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)-2-ethenyl-1,3-oxazol-5-yl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=C(C=2C(=CC=CC=2)Cl)N=C(C=C)O1 JJQOKUCYWIGCIN-UHFFFAOYSA-N 0.000 description 1
- AEEHOVNCLFTKTO-UHFFFAOYSA-N 4-[[benzyl(phenyl)hydrazinylidene]methyl]-n,n-diphenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)N=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 AEEHOVNCLFTKTO-UHFFFAOYSA-N 0.000 description 1
- SBMCZDLOXDWNIN-UHFFFAOYSA-N 4-[bis[4-(diethylamino)phenyl]methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 SBMCZDLOXDWNIN-UHFFFAOYSA-N 0.000 description 1
- QXOYFCJDRWUAMR-UHFFFAOYSA-N 4-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound C=1C2=CC=CC=C2C(O)=CC=1C(=O)NC1=CC=CC=C1 QXOYFCJDRWUAMR-UHFFFAOYSA-N 0.000 description 1
- FVGPNZKTTWPLOC-UHFFFAOYSA-N 9-ethyl-3-(2-phenylethenyl)carbazole Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=CC1=CC=CC=C1 FVGPNZKTTWPLOC-UHFFFAOYSA-N 0.000 description 1
- BODPVHGDJHVWAW-UHFFFAOYSA-N 9-ethyl-3-[2-(4-methoxyphenyl)ethenyl]carbazole Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=CC1=CC=C(OC)C=C1 BODPVHGDJHVWAW-UHFFFAOYSA-N 0.000 description 1
- SCHUFJWXJINKKV-UHFFFAOYSA-N 9-ethyl-3-fluoren-9-ylidene-2h-carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=C1C=C2C3=CC=CC=C3N(CC)C2=CC1 SCHUFJWXJINKKV-UHFFFAOYSA-N 0.000 description 1
- OBAPJZDFDIJDKV-UHFFFAOYSA-N C1=CC(N(CC)CC)=CC=C1C=C=NN(C)C1=CC=CC=C1 Chemical compound C1=CC(N(CC)CC)=CC=C1C=C=NN(C)C1=CC=CC=C1 OBAPJZDFDIJDKV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 241000270708 Testudinidae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- OHUWRYQKKWKGKG-UHFFFAOYSA-N formaldehyde;pyrene Chemical compound O=C.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 OHUWRYQKKWKGKG-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJVNNLDLHOFPFQ-UHFFFAOYSA-N n,n-dibenzyl-4-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(C=CC=2C=CC=CC=2)=CC=1)CC1=CC=CC=C1 OJVNNLDLHOFPFQ-UHFFFAOYSA-N 0.000 description 1
- IRKBOPBCDTWDDY-UHFFFAOYSA-N n,n-dibenzyl-4-[(diphenylhydrazinylidene)methyl]aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC(C=NN(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=1)CC1=CC=CC=C1 IRKBOPBCDTWDDY-UHFFFAOYSA-N 0.000 description 1
- BVTXDOPTUCCGGU-UHFFFAOYSA-N n,n-diethyl-4-(2-naphthalen-1-ylethenyl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC1=CC=CC2=CC=CC=C12 BVTXDOPTUCCGGU-UHFFFAOYSA-N 0.000 description 1
- UHVNFWQOSIZYQM-UHFFFAOYSA-N n,n-diethyl-4-(3-xanthen-9-ylideneprop-1-enyl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=CC=C1C2=CC=CC=C2OC2=CC=CC=C21 UHVNFWQOSIZYQM-UHFFFAOYSA-N 0.000 description 1
- GAZKGHIEJKXNCQ-UHFFFAOYSA-N n,n-diethyl-4-(4-phenyl-1,3-oxazol-2-yl)aniline Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NC(C=2C=CC=CC=2)=CO1 GAZKGHIEJKXNCQ-UHFFFAOYSA-N 0.000 description 1
- DXYYLUGHPCHMRQ-UHFFFAOYSA-N n,n-diphenyl-4-(2-phenylethenyl)aniline Chemical compound C=1C=CC=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 DXYYLUGHPCHMRQ-UHFFFAOYSA-N 0.000 description 1
- UAVOVDWXWRXKPS-UHFFFAOYSA-N n-[(4-methoxyphenyl)methylideneamino]-n-methylaniline Chemical compound C1=CC(OC)=CC=C1C=NN(C)C1=CC=CC=C1 UAVOVDWXWRXKPS-UHFFFAOYSA-N 0.000 description 1
- CEAPHJPESODIQL-UHFFFAOYSA-N n-[(9-ethylcarbazol-3-yl)methylideneamino]-n-phenylaniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 CEAPHJPESODIQL-UHFFFAOYSA-N 0.000 description 1
- ZQKFNYHHBMBPHU-UHFFFAOYSA-N n-benzyl-n-[(2,4-dimethoxyphenyl)methylideneamino]aniline Chemical compound COC1=CC(OC)=CC=C1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 ZQKFNYHHBMBPHU-UHFFFAOYSA-N 0.000 description 1
- HIWDRSNALOGCSA-UHFFFAOYSA-N n-benzyl-n-[(4-methoxynaphthalen-1-yl)methylideneamino]aniline Chemical compound C12=CC=CC=C2C(OC)=CC=C1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 HIWDRSNALOGCSA-UHFFFAOYSA-N 0.000 description 1
- RPHJRJPXKZMFFQ-UHFFFAOYSA-N n-benzyl-n-[(9-ethylcarbazol-3-yl)methylideneamino]aniline Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C=NN(C=1C=CC=CC=1)CC1=CC=CC=C1 RPHJRJPXKZMFFQ-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0679—Disazo dyes
- G03G5/0681—Disazo dyes containing hetero rings in the part of the molecule between the azo-groups
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0687—Trisazo dyes
- G03G5/0688—Trisazo dyes containing hetero rings
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0664—Dyes
- G03G5/0675—Azo dyes
- G03G5/0694—Azo dyes containing more than three azo groups
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Photoreceptors In Electrophotography (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3048644A JPH04211266A (ja) | 1986-06-05 | 1991-02-22 | 電子写真用感光体 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61-129082 | 1986-06-05 | ||
| JP12908286 | 1986-06-05 | ||
| JP3048644A JPH04211266A (ja) | 1986-06-05 | 1991-02-22 | 電子写真用感光体 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62503388A Division JPH0557581B1 (de) | 1986-06-05 | 1987-06-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04211266A JPH04211266A (ja) | 1992-08-03 |
| JPH0553266B2 true JPH0553266B2 (de) | 1993-08-09 |
Family
ID=15000634
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62503388A Pending JPH0557581B1 (de) | 1986-06-05 | 1987-06-04 | |
| JP3048644A Granted JPH04211266A (ja) | 1986-06-05 | 1991-02-22 | 電子写真用感光体 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62503388A Pending JPH0557581B1 (de) | 1986-06-05 | 1987-06-04 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4808503A (de) |
| EP (1) | EP0270685B1 (de) |
| JP (2) | JPH0557581B1 (de) |
| KR (1) | KR920001124B1 (de) |
| CA (1) | CA1302767C (de) |
| DE (1) | DE3750498T2 (de) |
| WO (1) | WO1987007736A1 (de) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4917981A (en) * | 1986-12-25 | 1990-04-17 | Fuji Electric Co., Ltd. | Photosensitive member for electrophotography |
| US4957837A (en) * | 1987-10-15 | 1990-09-18 | Fuji Electric Co., Ltd. | Photosensitive member for electrophotography containing hydrazone in charge transport layer |
| JP2656571B2 (ja) * | 1987-11-17 | 1997-09-24 | 三井東圧化学株式会社 | テトラフェニルチオフェン誘導体およびこれを含有する電子写真用感光体 |
| US4929525A (en) * | 1987-12-08 | 1990-05-29 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography containing azo or disazo compound |
| US4956277A (en) * | 1987-12-09 | 1990-09-11 | Fuji Electric Co., Ltd. | Photoconductor comprising charge transporting hydrazone compounds |
| DE3842872A1 (de) * | 1987-12-21 | 1989-06-29 | Fuji Electric Co Ltd | Photoleiter fuer die elektrophotographie |
| US4935323A (en) * | 1988-06-08 | 1990-06-19 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| JPH027061A (ja) * | 1988-06-27 | 1990-01-11 | Fuji Electric Co Ltd | 電子写真用感光体 |
| JPH0212258A (ja) * | 1988-06-30 | 1990-01-17 | Fuji Electric Co Ltd | 電子写真用感光体 |
| JP2629885B2 (ja) * | 1988-09-17 | 1997-07-16 | 富士電機株式会社 | 電子写真用感光体 |
| JP2629929B2 (ja) * | 1989-01-19 | 1997-07-16 | 富士電機株式会社 | 電子写真用感光体 |
| DE4001351C2 (de) * | 1989-01-19 | 1995-03-16 | Fuji Electric Co Ltd | Elektrophotographisches Aufzeichnungsmaterial |
| DE4042422C2 (de) * | 1989-03-29 | 1996-10-02 | Fuji Electric Co Ltd | Elektrophotographisches Aufzeichnungsmaterial |
| JPH02254467A (ja) * | 1989-03-29 | 1990-10-15 | Fuji Electric Co Ltd | 電子写真用感光体 |
| DE4042454C2 (de) * | 1989-06-06 | 1996-08-14 | Fuji Electric Co Ltd | Elektrophotographisches Aufzeichnungsmaterial |
| US5275898A (en) * | 1989-06-06 | 1994-01-04 | Fuji Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| JP2803169B2 (ja) * | 1989-06-06 | 1998-09-24 | 富士電機株式会社 | 電子写真用感光体 |
| DE4018010C2 (de) * | 1989-06-06 | 1995-04-27 | Fuji Electric Co Ltd | Elektrophotographisches Aufzeichnungsmaterial |
| US5266430A (en) * | 1989-06-06 | 1993-11-30 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| US5198318A (en) * | 1989-06-06 | 1993-03-30 | Fuji Electric Co., Ltd. | Bisazo photoconductor for electrophotography |
| US5132189A (en) * | 1989-09-07 | 1992-07-21 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| JPH03255453A (ja) * | 1990-01-17 | 1991-11-14 | Fuji Electric Co Ltd | 電子写真用感光体 |
| JP2770539B2 (ja) * | 1990-03-08 | 1998-07-02 | 富士電機株式会社 | 電子写真用感光体 |
| US5252416A (en) * | 1990-11-22 | 1993-10-12 | Fuji Electric Co., Ltd. | Photoconductor for electrophotography |
| JP2814739B2 (ja) * | 1990-11-22 | 1998-10-27 | 富士電機株式会社 | 電子写真用感光体 |
| US5316881A (en) * | 1991-12-27 | 1994-05-31 | Fuji Electric Co., Ltd. | Photoconductor for electrophotgraphy containing benzidine derivative |
| JPH05224439A (ja) * | 1992-02-12 | 1993-09-03 | Fuji Electric Co Ltd | 電子写真用感光体 |
| JP2817822B2 (ja) * | 1992-05-14 | 1998-10-30 | 富士電機株式会社 | 電子写真用感光体 |
| US20050277039A1 (en) * | 2004-06-10 | 2005-12-15 | Ramunas Lygaitis | Hydrazone-based charge transport materials having a bicyclic heterocyclic ring |
| US7220523B2 (en) * | 2004-06-10 | 2007-05-22 | Samsung Electronics Co., Ltd. | Bridged charge transport materials having two bicyclic heterocycle hydrazones |
| US7261987B2 (en) * | 2004-07-28 | 2007-08-28 | Samsung Electronics Co., Ltd | Azine-based charge transport materials having a bicyclic heterocyclic ring |
| US7351508B2 (en) * | 2004-10-12 | 2008-04-01 | Samsung Electronics Co., Ltd. | Organophotoreceptors with a charge transport material having multiple vinyl-containing hydrazone groups |
| US8911882B2 (en) * | 2006-09-28 | 2014-12-16 | Semiconductor Energy Laboratory Co., Ltd. | Stilbene derivative, light-emitting element, light-emitting device, and electronic device |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59204840A (ja) * | 1983-05-07 | 1984-11-20 | Konishiroku Photo Ind Co Ltd | 電子写真感光体 |
| JPS61117559A (ja) * | 1984-11-13 | 1986-06-04 | Fuji Photo Film Co Ltd | 光感応性組成物 |
| US4612271A (en) * | 1984-12-21 | 1986-09-16 | Fuji Photo Film Co., Ltd. | Photosensitive composition comprising azo compounds |
| JPH06247053A (ja) * | 1993-02-26 | 1994-09-06 | Ricoh Co Ltd | 感熱記録材料 |
-
1987
- 1987-06-04 CA CA000538844A patent/CA1302767C/en not_active Expired - Fee Related
- 1987-06-04 WO PCT/JP1987/000353 patent/WO1987007736A1/ja active IP Right Grant
- 1987-06-04 JP JP62503388A patent/JPH0557581B1/ja active Pending
- 1987-06-04 US US07/110,757 patent/US4808503A/en not_active Expired - Fee Related
- 1987-06-04 EP EP87903740A patent/EP0270685B1/de not_active Expired - Lifetime
- 1987-06-04 KR KR1019880700120A patent/KR920001124B1/ko not_active IP Right Cessation
- 1987-06-04 DE DE3750498T patent/DE3750498T2/de not_active Expired - Fee Related
-
1991
- 1991-02-22 JP JP3048644A patent/JPH04211266A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3750498D1 (en) | 1994-10-13 |
| KR880701401A (ko) | 1988-07-26 |
| EP0270685A1 (de) | 1988-06-15 |
| CA1302767C (en) | 1992-06-09 |
| JPH0557581B1 (de) | 1993-08-24 |
| WO1987007736A1 (en) | 1987-12-17 |
| KR920001124B1 (ko) | 1992-02-01 |
| DE3750498T2 (de) | 1995-02-09 |
| EP0270685A4 (de) | 1990-01-24 |
| JPH04211266A (ja) | 1992-08-03 |
| US4808503A (en) | 1989-02-28 |
| EP0270685B1 (de) | 1994-09-07 |
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